16 celebrity couples you never knew dated


Celebrity relationships tend to come and go pretty quickly, so unless you’re keeping up with your favorite idol, you’ve likely forgotten about most stars’ romantic pasts. But it’s fun to reminiscence about former duos, especially when they’ve completely escaped your memory — and feel pretty surprising now.

Here are some of our favorite celebrity couples you probably forgot about.

1. Madonna & Tupac Shakur

In 2015, Madonna admitted that she had dated Tupac in the early ’90s. The revelation made headlines. She even revealed that he had inspired her infamous, profanity-filled 1994 appearance on David Letterman.

madonna photo
Getty Images | Jason Merritt/TERM

Earlier this year, TMZ released a letter Tupac had written from jail to the famous songstress, expressing his sorrow about their breakup.

tupac photo
Getty Images | Rachel Murray

2. Sandra Bullock & Ryan Gosling

Although Sandra Bullock may have been 16 years older than Ryan Gosling, that didn’t stop the two from dating in 2002.

Getty Images

The two famous actors met after working together on the set of Murder By Numbers. However, their romance didn’t last long, after which he went on to date Rachel McAdams.

Kevin Winter/Getty Images

3. Ashton Kutcher & January Jones

It’s hard to picture Ashton Kutcher with anyone other than his wife Mila Kunis, but at point, he had a romance with actress January Jones.

ashton kutcher photo
Getty Images | Frazer Harrison

Kutcher was January Jones’s first boyfriend when she came to Los Angeles, but it sounds like her memories of him aren’t very fond. She told GQ magazine that he wasn’t supportive of her acting. Luckily, she still found success without him.

january jones photo
Getty Images | Alberto E. Rodriguez

4. Madonna & Dennis Rodman

Madonna sure had her fair share of famous romances. In addition to Tupac, Madonna also had a short tryst with Dennis Rodman.

madonna photo
Getty Images | Stephen Lovekin

They dated for a couple of months back in 1994. He even claimed that Madonna wanted to get pregnant with his child.

dennis rodman photo
Getty Images | Laura Cavanaugh

5. Cher & Tom Cruise

It seems that the age gap doesn’t mean much in Hollywood. Although she was 39 at the time, Cher was completely smitten for 23-year-old Tom Cruise back in the ’80s.

cher photo
Getty Images | Frazer Harrison

It seems wild to picture now, but they were once a happy couple. Cher has even called Tom Cruise one of her top five favorite former lovers. 

tom cruise photo
Getty Images | Jamie McCarthy

6. Ciara & Bow Wow

Ciara and Bow Wow did more than just collaborate on their 2005 song “Like You” — they also got together in real life. They met when they were 17 and Ciara was an extra in his tour.

ciara photo
Getty Images | Dimitrios Kambouris

Although they only dated for two years, they’re reportedly still close to this day.

bow wow photo
Getty Images | Frazer Harrison

7. Emily Blunt & Michael Bublé

This handsome couple dated for three years back in the late 2000s.

emily blunt michael buble photo
Getty Images | Evan Agostini

Although they may look picture perfect, it doesn’t look like things ended well between the two. There are rumors that Bublé cheated on the actress, although Blunt has chosen not to speak about the topic.

Evan Agostini/Getty Images

8. Britney Spears & Colin Farrell

Although no one has ever forgotten Britney Spears and Justin Timberlake, most people don’t seem to remember that the pop star dated Colin Farrell back in 2003.

colin britney photo
Getty Images | Kevin Winter

The pair was surprising given Spears’ wholesome image and Farrell’s bad boy reputation. Although their romance was short, sources close to the pop star speculate that Britney saw Colin as the one who got away.

colin britney photo
Getty Images | Kevin Winter

9. Mila Kunis & Macaulay Culkin

Before she settled down with Ashton Kutcher, Mila Kunis had a serious relationship with “Home Alone” star Macaulay Culkin.

macaulay culkin photo
Getty Images | Ethan Miller

Kunis has discussed how hard it was to date Culkin, since he was such a big celebrity at the time. Despite his crazed fans, they had a relationship for eight years until they split in 2011. It seems there is no bad blood, however, as Culkin recently congratulated Kunis on the birth of her baby. 

macaulay culkin photo
Getty Images | Handout

10. Wilmer Valderrama & Lindsay Lohan

Wilmer Valderrama is known for dating younger ladies — and not just his more recent girlfriend, Demi Lovato. Valderrama was also romantic with Lindsay Lohan.

lindsay lohan photo
Getty Images | Stuart C. Wilson

The two dated in 2004 when she was 17, and he was 24. The two kept their relationship quiet, however, until Lohan was 18.

wilmer valderrama photo
Flickr | Hot Rod Homepage

11. Kim Kardashian & Nick Cannon

Before she was the megastar that she is today, Kim Kardashian dated Nick Cannon from 2006 to 2007.

John M. Heller/Getty Images

However, according to Cannon, he broke up with her when he found out she lied about her infamous tape with Ray J. Cannon recently shared some throwback photos from their relationship, some of which include hangouts with other celebs like Paris Hilton and Lil’ Kim.

kim kardashian nick cannon photo
Getty Images | Ethan Miller

12. Sheryl Crow & Owen Wilson

Sheryl Crow and Owen Wilson dated from 1997-2000 after they met on the set of “The Minus Man.” From the looks of it, the duo wasn’t quite compatible, as the competition got too fierce.

sheryl crow photo
Getty Images | Andrew H. Walker

Crow spoke of her past relationships and said: “I have always gone out with guys who were highly successful, which would seem like it would put me at an equal level. But what ends up happening is that one of you becomes smaller — and it was always me.”

owen wilson photo
Getty Images | Frederick M. Brown

13. Gwyneth Paltrow & Brad Pitt

Back in the 90’s Gwyneth Paltrow and Brad Pitt were the ultimate power couple. They were even engaged!

gwyneth paltrow photo
Getty Images | Matthew Eisman

After meeting on the set of “Seven,” they dated for nearly three years before calling it quits. Luckily, there’s no bad blood, and they two are reportedly still friendly.

brad pitt photo
Getty Images | Tim P. Whitby

14. John Mayer & Jennifer Aniston

John Mayer has had his fair share of famous girlfriends, and Jennifer Aniston was no exception.

jennifer aniston john mayer photo
Getty Images | Michael Buckner

The singer and Friends’ actress dated for a couple years in the late 2000’s, but it did not end well. Aniston reportedly still dislikes Mayer, who broke things off for good in 2010.

jennifer aniston john mayer photo
Getty Images | Michael Buckner

15. Hilary Duff & Joel Madden

Although she was just a 16-year-old Disney starlet and he was a 25-year-old rockstar, Hillary Duff and Joel Madden dated for a few years back in the 2000s.

hilary duff joel photo
Getty Images | Peter Kramer

Despite the age difference, Duff called Madden “The most respectful boyfriend she has ever had.” She even said it took five or six dates before they ever kissed.

hilary duff joel photo
Getty Images | Mat Szwajkos

16. Nicky Hilton & Kevin Connolly

Nicky Hilton and “Entourage” star Kevin Connolly dated on and off for several years back in the early 2000s.

nicky hilton photo
Getty Images | Slaven Vlasic

Although Hilton was already well-known as an heiress, the two began dating when Connolly was a struggling actor. According to Connolly, their relationship was nothing but normal. “We watch ‘Desperate Housewives’ and fall asleep,” he told PEOPLE in 2005. 

kevin connolly photo
Getty Images | Alberto E. Rodriguez

Celebrities, Entertainment, Movies & TV
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About the Author
Carina Wolff
Carina is a health and wellness journalist based in Los Angeles. When she’s not writing, doing yoga, or exploring mountains and beaches, she spends her time cooking and creating recipes for her healthy food blog, Kale Me Maybe. Carina is also an ongoing writer for Bustle, Reader's Digest, FabFitFun, and more.

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